Tanabe Seiyaku Company, Limited

Masanori Inamasu

Kenji Tsujihara

Kenji Arakawa

Masakatsu Ozeki

Ikuo Iijima

Muneyoshi Ikezaki

Mitsuya Hongu

Nobuyuki Funami

Hajime Iwai

Kunihito Okumura

Tameo Iwasaki

Akio Ohtani

Takashi Nishitani

Takeshi Kanno

Katsuyuki Noguchi

Hisao Otsuka

Takashi Morita

A propiophenone derivative of the formula �I!: ##STR1## wherein X is O, S or methylene, OY is a protected or unprotected OH, Z is .beta.-D-glucopyranosyl or 4-O-(.alpha.-D-glucopyranosyl)-.beta.-D-glucopyranosyl or wherein one or more hydroxy groups of these groups may optionally be acylated, and the dotted line means the presence or absence of a double bond, or a pharmaceutically acceptable salt thereof. Said compounds have excellent hypoglycemic activity so that they are useful in the prophylaxis or treatment of diabetes.

Propiophenone derivative and a process for preparing the same

A method for prophylaxis or treatment of diabetes, which comprises administering to a patient with diabetes an effective amount of a dihydrochalcone derivative of the formula �I!: ##STR1## wherein Ar is an aryl group, R.sup.1 is hydrogen atom or an acyl group, R.sup.2 is a hydrogen atom, an acyl group or .alpha.-D-glucopyranosyl group, or R.sup.1 and R.sup.2 may combine together to form a substituted methylene group, R.sup.3 and R.sup.4 are each a hydrogen atom or an acyl group, OR.sup.5 is a protected or unprotected hydroxy group or a lower alkoxy group, or a pharmaceutically acceptable salt thereof.

Dihydrochalcone derivatives which are hypoglycemic agents

Novel butadiene derivatives of the formula [I]: ##STR1## wherein Ring A is tri-lower alkoxyphenyl, R.sup.1 and R.sup.2 combine each other to form a group of the formula: ##STR2## or one of R.sup.1 and R.sup.2 is lower alkoxy, and the other is group of the formula: -NHR.sup.3, in which R.sup.3 is hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkoxy, substituted or unsubstituted amino, hydroxy or pyridylcarbonyl, or salts thereof, these compounds have excellent antithrombotic activity and are useful as antithrombotic drug, or synthetic intermediate for preparing other antithrombotic drug.

Butadiene derivatives and process for using the same

Novel succinimide derivatives of formula I!: ##STR1## wherein Ring A is tri-lower alkoxyphenyl, R.sup.1 and R.sup.2 combine each other to form a group of the formula:

Succinimide derivatives and process for preparing the same

A method for treatment of diabetes, which comprises administering to a patient with diabetes an effective amount of a dihydrochalcone derivative of the formula: ##STR1## wherein Ar is an aryl group, R.sup.1 is a hydrogen atom or an acyl group, R.sup.2 is a hydrogen atom, an acyl group or .alpha.-D-glucopyranosyl group, or R.sup.1 and R.sup.2 may combine together to form a substituted methylene group, R.sup.3 and R.sup.4 are each a hydrogen atom or an acyl group, OR.sup.5 is a protected or unprotected hydroxy group or a lower alkoxy group; or a pharmaceutically acceptable salt thereof.

Novel benzoxazole derivatives of the formula: ##STR1## wherein R is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted cycloalkyl group or a substituted or unsubstituted heterocyclic group; Alk is single bond, a substituted or unsubstituted lower alkylene group, a lower alkenylene group or a lower alkynylene group; the group is a group of the formula: --CH.sub.2 -- or --CH.dbd., and a pharmaceutically acceptable salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as therapeutic agents for diabetes.

Benzoxazole derivatives

Novel benzoxazole derivative of the formula: ##STR1## wherein R is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted cycloalkyl group or a substituted or unsubstituted heterocyclic group; Alk is single bond, a substituted or unsubstituted lower alkylene group, a lower alkenylene group or a lower alkynylene group; the group ##STR2## is a group of the formula: --CH.sub.2 -- or --CH.dbd., and a pharmaceutically aceptable salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as therapeutic agents for diabetes.

Novel benzoxazine derivative of the formula: ##STR1## wherein R.sup.1 is phenyl group or a substituted thiazolyl group; R.sup.2 is hydrogen atom or a lower alkyl group; Q is single bond or a lower alkylene group, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as therapeutic agents for diabetes.

Benzoxazine derivatives

A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is the same as defined above, to give a compound of the formula: ##STR3## wherein R' and Ring A are the same as defined above, and when R' is benzyloxy, if required, further subjecting the compound [I'] to catalytic hydrogenation to give a compound of the formula: ##STR4## wherein Ring A is the same as defined above. The benzylalcohol derivative [I] is useful as an anti-diabetic agent.

Benzylalcohol derivative and process for preparing

A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, alkoxy of one to 4 carbon atoms or halogen, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, alkoxy of one to 4 carbon atoms or halogen, and Ring A is the same as defined above, and when R' is benzyloxy, if required, further subjecting the product to catalytic hydrogenation. The compounds (I) and pharmaceutically acceptable acid addition salts thereof are used as anti-diabetic agents.

Novel benzylalcohol derivative and process for preparing the same

Racemic or optically active .alpha.-(2,3,4-trimethoxyphenethylaminomethyl)-2-hydroxybenzylalcohol [I] may be prepared by condensing 2,3,4-trimethoxyphenethylamine with 2-benzyloxyphenylglyoxal or its hydrate, reducing the resultant .alpha.(2,3,4-tri-methoxyphenethylimino)-2-benzyloxyacetophenone to give .alpha.(2,3,4-trimethoxyphenethylaminomethyl)-2-benzyloxybenzylalcohol, if required, resolving the 2-benzyloxybenzylalcohol derivative into each of its optically active enantiomers, and subjecting the racemic modification or optically active enantiomer of said 2-benzyloxybenzylalcohol derivative to catalytic hydrogenation. The compound [I] and pharmaceutically acceptable acid addition salts thereof are useful as anti-diabetic agents. They may be also used in the treatment of thrombosis.

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Misato, Japan

Masanori Inamasu